Kiyoshi Mio-Imagn Images

Week 5 thrillers turn the pressure up on Bears' Caleb Williams vs Commanders

Originally posted on Chicago Bears on SI
By Pete Martuneac | Last updated Oct 7, 2025 8:58 AM ET

Caleb Williams may have said that he feels no pressure entering his second season, but both he and the Chicago Bears are under a metric ton of it after Week 5 of the 2025 NFL season. After two rough outings to start the Ben Johnson era, Williams delivered an epic Week 3 win over the Cowboys then guided the Bears through an ugly win over the Raiders in Week 4.

The Bears and Williams both look good at 2-2, but they're still lacking the one thing that would force the NFL to take them seriously: a signature win against a good team. The Cowboys may be a decent team, but they certainly weren't when they played the Bears. The Raiders are just a hot mess and Geno Smith is playing arguably the worst football of his career.

Yes, Williams desperately needs a signature win in 2025, especially after this past weekend. Three young quarterbacks, two from his own draft class, defeated true Super Bowl contenders and looked good doing it: Drake Maye downed the previously undefeated Buffalo Bills, Trevor Lawrence outdueled the mighty Patrick Mahomes, and Bo Nix led a furious fourth-quarter comeback over the defending champs.

In Week 6, Williams will get his chance to carry out a similar feat. The Bears must return to Washington to face the 3-2 Commanders, fresh off a huge 27-10 victory over the Chargers. Less than one year after the infamous 'Fail Mary' game that broke the 2024 Bears and precipitated a 10-game losing streak, the Bears will be right back where it happened, playing in front of the entire nation on Monday Night Football.

This is the perfect opportunity for Williams to deliver the kind of signature win that has thus far eluded him: a road game in prime time against a team that many NFL analysts believe is a Super Bowl contender. The best games of Williams' career can still be waved away by the doubters as empty wins over bad teams, and there's a kernel of truth here.

But if he can beat the Commanders in their own house and outduel Jayden Daniels, the 2024 NFL Offensive Rookie of the Year, in the process, that would leave no doubt. There'd be no hemming and hawing, no asterisks, nothing but concrete proof that Caleb Williams has arrived and that he's here to stay in Chicago.

Bears fans may not like it, and they may be in for a nerve-wracking game next Monday, but if Caleb Williams is who he is supposed to be, then Monday night will mark a turning point for this snakebitten franchise and officially usher in a new era.

This article first appeared on Chicago Bears on SI and was syndicated with permission.

More must-reads: